Grey was knighted in 1475 and was nominated four times to membership of The Most Noble Order of the Garter between 1476 and 1482. His political role also started in 1475, the year he was knighted, when he began to serve in Wales and the bordering English counties as part of the political rule of the council of his other half-brother, Edward, Prince of Wales (later Edward V). Grey served as a Justice of the Peace in Herefordshire from 1475 and sat at sessions of the peace in Hereford and Ludlow in 1476 and 1477.[1]

In 1479, he was appointed constable of Chester castle and in the same year was considered important enough for the city of Bristol to appeal to him for his aid. He served on a number of other judicial commissions in the region through the remainder of the reign of his stepfather. In 1482, he was granted the Welsh lordship of Kidwelly,[1] and in the same year was given a greater role in the upbringing of the Prince of Wales. Grey had become a very important person in Edward IV's rule in Wales and the bordering English counties. Grey was also being given a broader geographic field of activity, serving as constable of Wallingford Castle from 1482 and the following year being granted the Holland manors in Essex and Northamptonshire.[1]

After the death of Edward IV on 9 April 1483, and Grey's half-brother becoming Edward V, Grey's whole life soon fell apart due to the ruthlessness shown by his late stepfather's brother, Richard, Duke of Gloucester. On 30 April 1483, while accompanying Edward V to London from Wales with their uncle Anthony Woodville, 2nd Earl Rivers, Grey was arrested by Richard, Duke of Gloucester (later Richard III) at Stony Stratford and, with Rivers, imprisoned in the north of England. Within a few weeks, Grey's lands and offices had been redistributed to others, even though he had not legally been deprived of them.[citation needed] After Edward V was declared illegitimate, Richard, Duke of Gloucester, ascended to the throne as Richard III. Grey and his uncle were then executed at Pontefract Castle on 25 June 1483.[1] Richard Grey was aged around 26 at the time of his execution.